CN107250168A - Godied oil and preparation method thereof - Google Patents
Godied oil and preparation method thereof Download PDFInfo
- Publication number
- CN107250168A CN107250168A CN201680011958.8A CN201680011958A CN107250168A CN 107250168 A CN107250168 A CN 107250168A CN 201680011958 A CN201680011958 A CN 201680011958A CN 107250168 A CN107250168 A CN 107250168A
- Authority
- CN
- China
- Prior art keywords
- oil
- weight
- godied
- pitch
- godied oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000002360 preparation method Methods 0.000 title description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 65
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 57
- 239000011593 sulfur Substances 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 35
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 238000009826 distribution Methods 0.000 claims abstract description 21
- 230000004048 modification Effects 0.000 claims abstract description 19
- 238000012986 modification Methods 0.000 claims abstract description 19
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 17
- 235000019198 oils Nutrition 0.000 claims description 193
- 239000003921 oil Substances 0.000 claims description 192
- 239000011230 binding agent Substances 0.000 claims description 91
- 239000010426 asphalt Substances 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 241000196324 Embryophyta Species 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 20
- 230000000996 additive effect Effects 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000002156 mixing Methods 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 235000019486 Sunflower oil Nutrition 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000002600 sunflower oil Substances 0.000 claims description 15
- 235000019482 Palm oil Nutrition 0.000 claims description 12
- 239000002540 palm oil Substances 0.000 claims description 12
- 235000005687 corn oil Nutrition 0.000 claims description 11
- 239000002285 corn oil Substances 0.000 claims description 11
- 230000008929 regeneration Effects 0.000 claims description 10
- 238000011069 regeneration method Methods 0.000 claims description 10
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 10
- 239000005864 Sulphur Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- -1 diacylglycerol ester Chemical class 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- 229920001169 thermoplastic Polymers 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 240000008042 Zea mays Species 0.000 claims description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 4
- 239000004067 bulking agent Substances 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 230000001172 regenerating effect Effects 0.000 claims description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 235000009973 maize Nutrition 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- 239000010773 plant oil Substances 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 238000003892 spreading Methods 0.000 claims description 3
- 230000007480 spreading Effects 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- 150000003626 triacylglycerols Chemical class 0.000 claims description 3
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- 239000010499 rapseed oil Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
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- 230000000630 rising effect Effects 0.000 claims 2
- 240000000528 Ricinus communis Species 0.000 claims 1
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- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- 239000002383 tung oil Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 239000011295 pitch Substances 0.000 description 84
- 230000032683 aging Effects 0.000 description 42
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- 239000000047 product Substances 0.000 description 8
- 230000006866 deterioration Effects 0.000 description 7
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000787 lecithin Substances 0.000 description 5
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- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000004026 adhesive bonding Methods 0.000 description 3
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- 238000011068 loading method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
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- 238000012544 monitoring process Methods 0.000 description 2
- 229920001206 natural gum Polymers 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JSAIENUMNDAGTD-UHFFFAOYSA-N benzene ethene styrene Chemical compound C1=CC=CC=C1.C=C.C=C.C=CC1=CC=CC=C1 JSAIENUMNDAGTD-UHFFFAOYSA-N 0.000 description 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000008162 cooking oil Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
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- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
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- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
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- 238000005486 sulfidation Methods 0.000 description 1
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- 230000009466 transformation Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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- 238000004017 vitrification Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H3/00—Vulcanised oils, e.g. factice
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/02—Vulcanised oils, e.g. factice
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
- C08L95/005—Aqueous compositions, e.g. emulsions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L99/00—Compositions of natural macromolecular compounds or of derivatives thereof not provided for in groups C08L89/00 - C08L97/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D191/00—Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
- C09D191/02—Vulcanised oils, e.g. factice
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D195/00—Coating compositions based on bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D199/00—Coating compositions based on natural macromolecular compounds or on derivatives thereof, not provided for in groups C09D101/00 - C09D107/00 or C09D189/00 - C09D197/00
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F7/00—Chemical modification of drying oils
- C09F7/06—Chemical modification of drying oils by polymerisation
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- E—FIXED CONSTRUCTIONS
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- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C11/00—Details of pavings
- E01C11/005—Methods or materials for repairing pavings
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- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C7/00—Coherent pavings made in situ
- E01C7/08—Coherent pavings made in situ made of road-metal and binders
- E01C7/18—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders
- E01C7/26—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders mixed with other materials, e.g. cement, rubber, leather, fibre
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C7/00—Coherent pavings made in situ
- E01C7/08—Coherent pavings made in situ made of road-metal and binders
- E01C7/18—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders
- E01C7/26—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders mixed with other materials, e.g. cement, rubber, leather, fibre
- E01C7/262—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders mixed with other materials, e.g. cement, rubber, leather, fibre with fibrous material, e.g. asbestos; with animal or vegetal admixtures, e.g. leather, cork
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
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Abstract
As described herein is a kind of biorenewable of polymerization, previous modification or function carburetion, it includes the polydispersity index that distribution of polymer, scope with about 2 weight % to about 80 weight % oligomer are about 1.30 to about 2.20, and the sulfur content that scope is 0.001 weight % to about 8 weight %.Also describe the method for manufacturing the godied oil and being incorporated into bituminous pavement road, paving roof and application.
Description
The cross reference of related application
This application claims the rights and interests for the U.S. Patent Application No. 62/126,064 submitted for 27th for 2 months in 2015, the Shen
It please be incorporated herein in its entirety by reference.
Technical field
This disclosure relates to godied oil and for godied oil and with pitch be blended with strengthen pitch (asphalt) and/or
The method of the performance on the road surface containing recycling and aging asphalt material.
Background technology
The overall performance that the technological challenge that asphalt industry faces recently has been used for pitch to introduce the product based on agricultural increases
Create chance by force.This performance enhancement may include to expand the usable temp interval (UTI) of pitch, rejuvenating aged pitch and
Increase-volume elastomeric thermoplastic polymers in pitch.
Brief summary of the invention
Herein described aspects provide a kind of godied oil, and it includes the oligomer with about 2 weight % to about 80 weight %
Distribution of polymer, the scope of content are the polydispersity index of about 1.30 to about 2.20, and scope is 0.001 weight % to about 8
Weight % sulfur content.
Other aspects as described herein provide a kind of methods of godied oil, it is included biorenewable, previously modification or
Function carburetion is heated at least 100 DEG C, adds sulfur-containing compound into the oil of heating, and make the sulfur-containing compound with it is described
Oil reaction is to produce godied oil, and the godied oil includes the polymerization to about 80 weight % oligomer with about 2 weight %
Thing distribution, the polydispersity index that scope is about 1.30 to about 2.20, and the sulphur that scope is 0.001 weight % to about 8 weight %
Content.
As described herein and other aspects provide the godied oil mixing in bituminous pavement road, paving roof and application
Enter.
Accompanying drawing is described
Fig. 1 and Fig. 2 show the complex modulus curve of the function as the Loading frequency reduced of pitch.
Fig. 3 shows comparisons of the DSC than heating curve.
Specific embodiment
" flash-point " or " flash temperature " is measuring for the minimum temperature that material is initially glistened with of short duration flame.It is according to ASTM
D-92 method is measured using Cleveland open cup (Cleveland Open Cup), and with degree Celsius (DEG C) report.
" oligomer " is defined as the polymer of the number-average molecular weight (Mn) more than 1000.Other are any for monomer composition
Material, and including monoacylglycerol ester (MAG), diacylglycerol ester (DAG), triacylglyceride (TAG) and free-fat
Sour (FFA).
" performance rate " (PG) is defined as the temperature interval designed for specific asphaltic products.For example, designed for suitable
Answer the asphaltic products of 64 DEG C of high temperature and -22 DEG C of low temperature that there is 64-22 PG.Performance rate standard is by U.S. state highway and fortune
Defeated official association (Performance Grade standards are set by America Association of
State Highway and Transportation Officials) (AASHTO) and American Society for Testing Materials
(American Society for Testing Materials) (ASTM) is formulated.
" polydispersity index " (also referred to as " molecular weight distribution ") is the ratio of weight average molecular weight (Mw) and number-average molecular weight (Mn)
Rate.Polydispersity number is collected using the gel permeation chromatography instrument equipped with the pumps of Waters 510 and 410 differential refractometers
According to.Sample is prepared with about 2% concentration in THF solvents.Use the flow velocitys of 1ml/ minutes and 35 DEG C of temperature.Post by
50th, 100,5 microns of linear/hybrid protection posts of Phenogel and 300x 7.8mm Phenogel 5 under 1000 and 10000 angstroms
Micron post (styrene diethylene benzene copoly mer) composition.Use following standard test molecular weight：
" usable temp interval " (UTI) be defined as the maximum temperature and the minimum temperature that design for specific asphaltic products it
Between interval.For example, there is 86 UTI designed for adapting to the asphaltic products of 64 DEG C of high temperature and -22 DEG C of low temperature.For road
Road laying is applied, and the seasonality of temperature and geographical extreme condition will determine to be directed to the UTI that asphaltic products must be designed.By by
A series of AASHTO of SHRP (Strategic Highway Research Program) (SHRP) exploitation
Test (also referred to as " grading performance " (PG) specification) to determine the UTI of pitch with ASTM standard.
Pitch and asphalt material
For purposes of the present invention, pitch, asphalt binder and asphalt (bitumen) refer to the combination of bituminous paving
Phase.Asphalt material can refer to the blend of asphalt binder and other materials (such as gathering materials or filler).Used in the present invention
Binder can be from Asphalt Production production of sperm refinery, slag making, refinery's vacuum column tower bottom distillate, asphalitine (pitch) and true
The material that other residues of void tower tower bottom distillate processing are obtained, and from such as recovery bituminous paving (RAP) and recycling
The oxidation of the recycling asphalt material of bituminized shingle (RAS) and aged asphalt.
Originate oil plant
Biorenewable oil can be used as originating oil plant.Biorenewable oil can be included from the separation of plant, animal and algae
Oil.
Oily example based on plant may include but be not limited to soybean oil, Linseed oil, Tower rape oil, rapeseed
Oil, castor oil, tall oil, cottonseed oil, sunflower oil, palm oil, peanut oil, safflower oil, corn oil, maize alcohol stillage oil, lecithin
Fat (phosphatide) and combinations thereof and rough stream.
Oily example based on animal may include but be not limited to animal tallow (for example, lard, tallow) and lecithin (phosphorus
Fat) and combinations thereof and rough stream.
Biorenewable oil can also include part hydrogenated oil and fat, the oil with conjugated bonds and wherein be not introduced into heteroatomic thick
Carburetion, such as, but not limited to diacylglycerol ester, monoacylglycerol ester, free fatty, the Arrcostab of aliphatic acid are (for example, first
Ester, ethyl ester, propyl ester and butyl ester), glycol and three alcohol esters (for example, ethylene glycol, propane diols, butanediol, trimethylolpropane) and its
Mixture.The example of biorenewable oil can be waste cooking oil or other used oils.
Previous modification or function carburetion also are used as originating oil plant.The example of previous modified oil is previously poly- by other
Conjunction technology vulcanize or polymerization those, such as maleic anhydride or it is acrylic acid modified, hydrogenation, it is dicyclic pentylene modified, by with iodine
Reaction and be conjugated, ester exchange or be processed to change acid number, hydroxyl value or other characteristics.Some examples of previous modified oil are many
First alcohol ester, such as polyglycerol ester or castor oil ester or polylactone.Such modified oil can with it is unmodified based on plant oil or
Oil, aliphatic acid, glycerine and/or lecithin blending based on animal.The example of function carburetion be wherein have been introduced into hetero atom (oxygen,
Nitrogen, sulphur and phosphorus) those.
Preferred in terms of, starting oil plant be reclaim corn oil (generally by by corn transformation into ethanol manufacturing process
The residual liquid of generation) (also referred to as " maize alcohol stillage oil ") or other inexpensive waste oil.In terms of another is preferred, starting oil
Material includes free fatty.It would be recognized by those skilled in the art that if necessary to higher feature, then can be used with higher
The oil based on plant of degree of unsaturation level.
Oily is sulfur-crosslinked
In all fields, it is contained by using sulfur-containing compound crosslinked bio is renewable, in previous modification or function carburetion
Fatty acid chain and/or the glyceride fractions of triglyceride molecules realize biorenewable, previous modification or function carburetion
Polymerization.Sulphur in sulfur-containing compound is preferably reduction form.Polymerization comprises the following steps：(a) heating biological it is renewable,
Previous modification or function carburetion, (b) add sulfur-containing compound into the oil of heating, and (c) makes the sulfur-containing compound and institute
State oil reaction with produce have required distribution of polymer (oligomer with about 2 weight % to about 80 weight %), many points
Dissipate index (about 1.30 to about 2.20) and the godied oil of sulfur content (between about 0.01 weight % and about 8 weight %).
In the first step, biorenewable, previous modification or function carburetion are in the vessel in heating equipped with agitator
To at least 100 DEG C.At preferred aspect, biorenewable, previous modification or function carburetion (also can be collectively referred to as herein " oil ")
It is heated at least 115 DEG C.Preferred in terms of, sulfur-containing compound is added gradually to the biorenewable of heating, previously changed
Property or function carburetion in, and can with solid or melting form add, it should be understood, however, that can before oil or with oil simultaneously addition
Sulfur-containing compound.Preferred in terms of, sulfur-containing compound can be elementary sulfur, but not limited to this.In reaction between sulphur and oil
Increase the temperature of oil-sulphur mixture on ground, and preferred in terms of, during course of reaction, reaction is maintained at about 130 DEG C
With about 250 DEG C between, between more preferably from about 130 DEG C and about 220 DEG C and between even more preferably about 160 DEG C and about 200 DEG C
Temperature.
During polymerisation between oil and sulphur, oil-sulphur mixture can be continuously sprayed with stream containing gas.Gassiness
Body stream may be selected from the group being made up of nitrogen, air and other gases.Stream containing gas can may advantageously facilitate reaction, and can also help
In the smell (H related to reaction of reduction in the final product2S and other sulfide).The use of air can be beneficial, because
It can cause the oily oxidation polymerization in addition to sulfidation.
It is optionally possible to improve reaction rate using accelerator.The example of accelerator includes but is not limited to zinc oxide, oxygen
Change magnesium, dithiocar-bamate.
Reaction can proceed with, and gel permeation chromatography (GPC) and/or viscosity can be used to carry out continuous monitoring, until
The degree of polymerization needed for realizing, as discussed below.
Compared with other method, the robustness of sulfur-crosslinked reaction and for polymerization contain high free fatty acid content using it
It is the advantage of this polymerization with the ability of the lower cost raw material of residual moisture, so as to provide the flexible of parent material selection
Property.
Polymerization property
The reaction between sulfur-containing compound and biorenewable, previous modification or function carburetion is driven, is had until realizing
Oligomer (20 weight % to 98 weight % monomers) between about 2 weight % and about 80 weight %, and more preferably from about 15 weights
Measure the oligomer (40 weight % to 85 weight % monomers) between % and about 60 weight %, and even more preferably about 20 weights
Measure the distribution of polymer of the oligomer (40 weight % to 80 weight % monomers) between % and about 60 weight %.Even more excellent
The aspect of choosing, the oligomer and about 25 weight % that distribution of polymer scope is about 50 weight % to about 75 weight % to about 50 weights
Measure % monomer.
The polydispersity index scope of godied oil is about 1.30 to about 2.20, and more preferably from about 1.50 to about 2.05.
The benefit of reaction described here is the low sulfur content in gained godied oil.In some respects, sulfur content accounts for polymerization
Oily is less than 8 weight %.In other respects, sulfur content account for godied oil be less than 6 weight %.In terms of other, sulfur content is accounted for again
Godied oil be less than 4 weight %.And in other respects, sulfur content account for godied oil be less than 2 weight %.However, sulfur content is accounted for
At least 0.001 weight % of godied oil.
The flash-point of gained godied oil as measured by using Cleveland open cup method is at least about 100 DEG C and not surpassed
Cross about 400 DEG C.In some respects, the flash-point of godied oil is between about 200 DEG C and about 350 DEG C.In other respects, the sudden strain of a muscle of godied oil
Point is between about 220 DEG C and about 300 DEG C.It yet still another aspect, the flash-point of godied oil is between about 245 DEG C and about 275 DEG C.This paper institutes
The godied oil stated can have the flash-point higher compared with beginning oil plant, particularly when compared with other polymerization techniques.
The viscosity of godied oil will according to starting oil plant type and change, but generally at 100 DEG C scope be about 1cSt extremely
About 100cSt.
Final use application
On the one hand, the present invention provides a kind of asphalt binder and 0.1 weight for including 60 weight % to 99.9 weight %
% is measured to the 40 weight % modified pitch of blend of godied oil and preparation method thereof, wherein by as described above sulfur-crosslinked
Realize the polymerization of oil.Modified pitch can be used for paving the way or spreading rooftop applications.
On the other hand, the present invention provides a kind of asphalt binder and 0.1 weight for including 60 weight % to 99.9 weight %
% is measured to the 40 weight % modified pitch of blend of godied oil and preparation method thereof, wherein godied oil be as described above by
The godied oil of sulfur-crosslinked realization and above-mentioned biorenewable, previous modification or function carburetion are (for example：It is unmodified based on plant
In oil, the oil based on animal, aliphatic acid, fatty acid methyl ester, natural gum or lecithin, and modified oil or other oil or aliphatic acid
Natural gum or lecithin) in one or more blends.
In addition to godied oil, other components can be combined to produce modified pitch with asphalt binder, such as, but not limited to
Thermoplastic elastomer (TPE) and thermoplastic polymer (s-B-S, vinyl acetate-vinyl ester, functionalised polyolefin etc.
Deng), polyphosphoric acid, antistripping additive (based on amido, based on phosphate etc.), warm-mixing additive, emulsifying agent and/or fibre
Dimension.Generally, these components are added to asphalt binder/godied oil by about 0.1 weight % to about 10 weight % dosage of scope
In.
Asphalt modification
The need for the decline of asphalt quality has promoted addition chemical modifier to improve asphaltic products quality.From oil
The black mineral oil of refining is the most frequently used modifying agent.These mineral oil are by making binder " plasticising " extend the temperature of asphaltic products
Lower limit is spent, but this also tends to reduce the temperature upper limit of pitch.
Bitumen dilution mineral oil (Mineral flux oil), the crude oil distillate based on oil and refined mineral oil has been again
It is attempted for soft pitch.Generally, the high-temperature modulus with low-temperature phase than pitch are caused to reduce using this material so that pitch
It is easier to form rut at high temperature.Such effect causes usable temp interval (UTI) reduction.
Bitumen dilution mineral oil, the crude oil distillate based on oil and again refined mineral oil pavement construction temperature (for example,
150 DEG C to 180 DEG C) under generally there is volatile part, generally there is the flash-point lower than pitch, and may be old due to oxidation
Change and be easy to produce higher performance loss.
Godied oil and blend as described herein are not only the viable substitute of mineral oil, but also are proved to and other property
Energy modifying agent, which is compared, can expand to the UTI of pitch bigger degree, therefore provide sizable value for asphalt manufacturers.Make
It is to soften additive (such as flux oil, fuel in other pitches with the UTI increases observed by godied oil as described herein
Oil or flushing oil) in the unique property that has no.Generally, the godied oil by the weight % of pitch emphasis gauge about 2 to 3 weight % is passed through
Realize that one-level is improved in SHRP grading performances (PG) specification or infiltration hierarchy system that use in many countries.For example, for
About 3 weight % godied oil addition, it can be seen that up to 4 DEG C of UTI increases, therefore the wider PG of offer is modified scope,
So that low side temperature can be with relatively low without sacrificing higher high-end temperature.
The regeneration of aging asphalt material
Pitch is mainly aoxidized and progress " aging " of volatilizing by the combination of mechanism.Aging increase asphalt modulus, reduction are viscous
Property dissipate and stress relaxation, and increase fragility under relatively low performance temperature.Therefore, pitch becomes easier to rupture and damaged
Accumulation.Containing from the height aged asphalt binder for such as reclaiming bituminous paving (RAP) and recycling bituminized shingle (RAS) source
Recycling and recovery asphalt material usage amount it is more and more, generated for can partially or completely recover old
The need for changing the rheology of pitch and " regenerative agent " of fracture characteristics.The aging of pitch also has been demonstrated may be little by little by increase
Related HMW and the content of highly polar insoluble " asphalitine " part increase the unstability and phase incompatibility of colloid.
The purposes of godied oil as described herein is particularly suitable for use in RAP and RAS applications.Godied oil described in this document serves as pitch part
Bulking agent, particularly in aging and oxidized asphalt so that balance and stable asphalt binder have the performance recovered and
Durability.
In process of factory production, pitch is exposed to high temperature (be usually 150 DEG C to 190 DEG C between) and exposed to sky
Gas, may occur the notable oxidation and volatilization of lighter part during this period, so as to cause modulus increase and viscous behavior reduction.Make
With rolling film baking oven (ASTM D2872) imitated aging process, during this period, the rolling film of pitch is subjected at about 163 DEG C
Heated air jets about 85 minutes.Follow ASTM D7175 and use the stream before and after dynamic shear rheometer measurement ageing process
Become characteristic, before and after aging | G*|/sin δ ratio, wherein G*It is complex modulus, and δ is phase angle.After aging (|
G* |/sin δ) it is bigger with the ratio of (| G* |/sin δ) before aging, the influence of deterioration by oxidation and volatilization to being tested pitch is bigger.
Using this program, show that the pitch handled with heretofore described godied oil or its blend has relatively low
Ratio, therefore show that the trend that changes rheological behavior is relatively low due to deterioration by oxidation and volatilization.
Therefore, godied oil as described herein, which has been shown, can regenerate aged asphalt binder, and change less aging
The rheological behavior of asphalt binder.Therefore, it is possible to use the aging of high content is recycled asphalt material by low dose of godied oil
Mix in road and other application, so as to produce by reducing the use of new resources and significantly economical save and road may be reduced
In face of the influence of environment.
Compatibilization of the elastomeric thermoplastic polymers in pitch
Pitch is generally carried out with thermoplastic elastomer (TPE) and thermoplastic polymer (such as s-B-S (SBS))
Modified, to increase high-temperature modulus and elasticity, so as to increase the resistance to heavy traffic load, and toughness reinforcing bitumen base is to resist
Due to damage accumulation caused by repeated load.Such polymer is generally made in pitch with 3 weight % to 7 weight % dosage
With, and high shear is blended into pitch and causes its at similar temperature " solidification " at a temperature of more than 180 DEG C, herein
Period, polymer is swelled until realizing continuous volume phase in pitch by adsorbing lighter part in pitch.
The volume for the polymer being fully cured is by by the thin of compatibility of the polymer in pitch and discrete particles
The influence of degree, therefore can by increasing the interface surface between pitch and polymer and adding that specific surface area and enhancing is swelled
Can property.
The godied oil described in this document is added and is blended into pitch when before incorporation polymer or cure stage
When, the oil shown can in pitch further increase-volume elastomer polymer.This for elastomer polymer not right and wrong
Chang Xiangrong asphalt binder will be particularly effective.In addition, the oil potentially contributes to be swelled polymer during curing
Lighter part.
Warm-mixing additive and pitch
In recent years, increasing road surface part using the additive of commonly known as " warm-mixing additive " to produce to produce
Raw " warm mix " bituminous paving..Warm mix road surface can produce at a temperature of relatively low production and be compacted, realize target mixture density
Less compaction force is needed, and therefore can keep the characteristic needed for the compacting under lower temperature, so as to increase pitch
Maximum transportation range of the mixture from factory to job site.
Warm-mixing additive provide benefit different mechanisms be included in asphalt mixture compacting process increase gather materials lubricity,
Binder viscosity at a temperature of reduction production, and make the coating gathered materials and wetability more preferably.Therefore, when be added to pitch mixing
When in thing, various chemicals and additive can show to be attributed to one or more characteristics of warm-mixing additive.
Godied oil as described herein may be used as warm-mixing additive and/or compacting auxiliary agent, to realize that expection adds from warm mix
Plus many benefits of agent, including minimally reduce production and construction temperature by increasing gather materials lubricity and wetability of gathering materials.
In this application, the dosage of additive is preferably between asphaltic about 0.1 weight % and 2 weight %.
Embodiment
Following examples are presented to illustrate the present invention and help those of ordinary skill to manufacture and using the present invention.The reality
Example is applied to be not intended to limit the scope of the present invention in addition in any way.
Experimental method
The charging of precipitated sulfur (mass range is between 6.5 grams to 56.5 grams) is added to 1 liter containing 650 grams of vegetable oil
In round-bottomed flask.Then reactor is heated to goal response temperature using heating mantles, be careful not to exceed 5 DEG C of target temperature with
On.Reactant mixture is stirred using the electric mixer with agitating shaft and blade.With nitrogen with 2-12 standard cubic foots/small
When (SCFH) continuously spray the reaction.Any distillate is collected with condenser and reception flask.
It should be noted that when sulphur is incorporated in oil, about 110 DEG C -115 DEG C of foam will be produced by reacting.It is anti-using GPC monitorings
Should be to measure oligomer and distribution, and measure viscosity at 40 DEG C using ASTM D445.When the oligomer needed for realization
During content, reaction is considered as complete.Then reactor is cooled to 60 DEG C.
Embodiment 1：The pitch being modified with polymeric palm oil #1
A kind of modified asphalt binders, it is included：
97.0 weight % pure (i.e. unmodified) asphalt binder, it is classified as PG64-22 standard class (and PG
64.88-24.7 " true " grade) note：True grade represents that pitch meets the accurate temperature of control normal value, and it always reaches
Arrive and exceed corresponding standard class (that is, real high thermal level will be always above standard high temperature grade, and real low temperature
Grade will always be less than standard cryogenic grade).
3.0 weight % vulcanization refined palm oil, its elementary sulfur under nitrogen jet with 3 weight % is at 160 DEG C
Reaction 5 hours.This is obtained with following modifying agent：
The oligomer of ο 31.8%
ο is 17.2cSt viscosity at 100 DEG C
ο about 1.30 polydispersity index (PDI)
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Entered according to AASHTO M320
Row performance rate is tested.The modified low-temperature grade for producing 4.8 DEG C is improved, and PG 64-22 pure binder grade is changed into PG 58-
28.High performance level and the net change of low performance levels cause usable temp interval to improve 0.8 DEG C.Details is shown in Table 1.
Table 1
1UTI：As determined using AASHTO M320, difference between high-temperature behavior grade and cryogenic property grade is used as
Usable temp interval.
2O-DSR：Such as follow ASTM D7175 and AASHTO M320 and use the not old of dynamic shear rheometer (DSR) measurement
Change the high-temperature behavior grade of (" original ") asphalt binder.
3R-DSR：Such as follow the rolling that ASTM D7175 and AASHTO M320 use dynamic shear rheometer (DSR) to measure
The high-temperature behavior grade of thin film oven aging (RTFO, it then follows ASTM D2872) asphalt binder.
4S-BBR：ASTM D6648 and AASHTO M320 are such as followed using bending mechanical properties to being dried using rolling film
Both case (ASTM D2872) and pressure aging vessel PAV (ASTM D6521) regulation asphalt binder measurement by creep stiffness
The cryogenic property grade of parameter (" S ") control.
5m-BBR：ASTM D6648 and AASHTO M320 are such as followed using bending mechanical properties to being dried using rolling film
Both case (ASTM D2872) and pressure aging vessel PAV (ASTM D6521) regulation asphalt binder measurement by creep rate
The cryogenic property grade of parameter (" m " value) control.
Embodiment 2：The pitch being modified with polymeric palm oil #2
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
3.0 weight % vulcanization refined palm oil, its elementary sulfur under nitrogen jet with 4 weight % is at 160 DEG C
Reaction 20.5 hours.This is obtained with following modifying agent：
The oligomer of ο 56.18%
ο is 25.0cSt viscosity at 100 DEG C
ο about 1.50 PDI
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Entered according to AASHTO M320
Row performance rate is tested.The modified low-temperature grade for producing 5.9 DEG C is improved, and PG 64-22 pure binder grade is changed into PG 58-
28.High performance level and the net change of low performance levels cause usable temp interval to improve 1.5 DEG C.Details is shown in Table 2.
Table 2
Embodiment 3：The pitch that corn oil #1 is modified is reclaimed with vulcanization
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
Corn oil (RCO) is reclaimed in 3.0 weight % vulcanization, and its elementary sulfur with 1.5 weight % under nitrogen jet exists
Reacted 7 hours at 160 DEG C.This is obtained with following modifying agent：
The oligomer of ο 16.0%
ο about 1.50 PDI
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Entered according to AASHTO M320
Row performance rate is tested.The modified low-temperature grade for producing 6.0 DEG C is improved, and PG 64-22 pure binder grade is changed into PG 58-
28.High performance level and the net change of low performance levels cause usable temp interval to improve 0.4 DEG C.Details is shown in Table 3.
Table 3
Embodiment 4：The pitch that corn oil #2 is modified is reclaimed with vulcanization
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
Corn oil (RCO) is reclaimed in 3.0 weight % vulcanization, and its elementary sulfur with 6.0 weight % under nitrogen jet exists
Reacted 6 hours at 160 DEG C.This is obtained with following modifying agent：
The oligomer of ο 50.3%
ο is 270cSt viscosity at 40 DEG C
ο about 2.19 PDI
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Entered according to AASHTO M320
Row performance rate is tested.The modified low-temperature grade for producing 4.4 DEG C is improved, and PG 64-22 pure binder grade is changed into PG 58-
28.High performance level and the net change of low performance levels cause usable temp interval to improve 0.7 DEG C.Details is shown in Table 4.
Table 4
Embodiment 5：The pitch being modified with vulcanization refined sunflower oil blend #1
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
3.0 weight % blend, it has：
The weight % of ο 14.5 vulcanization refined sunflower oil, its elementary sulfur under nitrogen jet with 7.0 weight % is 160
Reacted 19 hours at DEG C.This obtains the modifying agent with 70.8% oligomer
The weight % of ο 85.5 refined sunflower oil
ο sulfurized oils and unmodified oily blend have 11.9% oligomer, the gluing for 55cSt at 40 DEG C
Degree, and about 1.64 PDI.
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Entered according to AASHTO M320
Row performance rate is tested.The modified low-temperature grade for producing 5.3 DEG C is improved, and PG 64-22 pure binder grade is changed into PG 58-
28.The net change of high low performance levels and low performance levels, which produces complete low-temperature grade, to be improved, and usable temp interval does not have
Change.Details is shown in Table 5.
Table 5
Embodiment 6：The pitch being modified with vulcanization refined sunflower oil blend #2
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
3.0 weight % blend, it has：
The weight % of ο 53.9 vulcanization refined sunflower oil, its elementary sulfur under nitrogen jet with 7.0 weight % is 160
Reacted 19 hours at DEG C.This obtains the modifying agent with 70.8% oligomer
The weight % of ο 46.1 refined sunflower oil
ο sulfurized oils and unmodified oily blend have 42.76% oligomer, the gluing for 177Cst at 40 DEG C
Degree, and about 3.16 PDI.
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.It is modified the low of 4.8 DEG C of generation
Warm grade is improved, and PG 64-22 pure binder grade is changed into PG 58-28.Performance rate survey is carried out according to AASHTO M320
Examination.High performance level and the net change of low performance levels cause usable temp interval to improve 0.1 DEG C.Details is shown in Table 6.
Table 6
Embodiment 7：The pitch being modified with vulcanization refined sunflower oil blend #3
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
3.0 weight % blend, it has：
The weight % of ο 63.4 vulcanization refined sunflower oil, its elementary sulfur under nitrogen jet with 7.0 weight % is 160
Reacted 19 hours at DEG C.This obtains the modifying agent with 70.8% oligomer
The weight % of ο 36.6 refined sunflower oil
ο sulfurized oils and unmodified oily blend have 48.3% oligomer, the gluing for 254Cst at 40 DEG C
Degree, and about 3.55 PDI.
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Entered according to AASHTO M320
Row performance rate is tested.The low-temperature grade of modified production producing 75 deg. C is improved, and PG 64-22 pure binder grade is changed into PG 58-
28.High performance level and the net change of low performance levels cause usable temp interval to improve 0.8 DEG C.Details is shown in Table 7.
Table 7
Embodiment 8：The pitch being modified with refined sunflower oil and palm oil #1 blend
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
3.0 weight % blend, it has：
The weight % of ο 14.5 vulcanization refined sunflower oil, its elementary sulfur under nitrogen jet with 7.0 weight % is 160
Reacted 19 hours at DEG C.This obtains the modifying agent with 70.8% oligomer
The weight % of ο 84.5 palm oil
The blend of ο sulfurized oils and palm oil has about 11.9% oligomer
ο about 1.77 PDI
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Entered according to AASHTO M320
Row performance rate is tested.The low-temperature grade of modified production producing 75 deg. C is improved, and PG 64-22 pure binder grade is changed into PG 58-
28.High performance level and the net change of low performance levels cause usable temp interval slightly to reduce 0.2 DEG C.Details is shown in table 8
Go out.
Table 8
Embodiment 9：The pitch being modified with the blend of vulcanization refined sunflower oil and palm oil #2
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
3.0 weight % blend, it has：
The weight % of ο 59.0 vulcanization refined sunflower oil, its elementary sulfur under nitrogen jet with 7.0 weight % is 160
Reacted 19 hours at DEG C.This obtains the modifying agent with 70.8% oligomer
The weight % of ο 41.0 palm oil
The blend of ο sulfurized oils and palm oil has about 43% oligomer and about 2.37 PDI
After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Entered according to AASHTO M320
Row performance rate is tested.The modified low-temperature grade for producing 4.2 DEG C is improved, and PG 64-22 pure binder grade is changed into PG 58-
28.High performance level and the net change of low performance levels cause usable temp interval slightly to reduce 0.1 DEG C.Details is shown in table 9
Go out.
Table 9
Embodiment 10：With the modified pitch of sulfurized soybean acid oil (also referred to as " soap stock of acidifying ")
A kind of modified asphalt binders, it is included：
97.0 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
3.0 weight % vulcanization Refined Soybean acid oil, its elementary sulfur under nitrogen jet with 5.0 weight % is at 160 DEG C
Lower reaction 8 hours.This obtain with 28.14% oligomer, at 40 DEG C be 167cSt viscosity, and about 2.36 PDI
Modifying agent.After binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.According to AASHTO M320
Carry out performance level estimate.The modified low-temperature grade for producing 3.3 DEG C is improved, and PG 64-22 pure binder grade is changed into PG
58-28.High performance level and the net change of low performance levels cause usable temp interval to reduce 1.5 DEG C.This embodiment is strong
Adjusted free fatty acid content to be not intended to influence to the potential of modifying agent performance because with terms of the high thermal level caused by under
Drop is compared, substantially less effective in terms of cryogenic property grade is improved.Details is shown in Table 10.
Table 10
Embodiment 11：The pitch that corn oil #1 is modified as solubilizer is reclaimed with styrene butadiene styrene and vulcanization
A kind of modified asphalt binders, it is included：
92.41 weight % pitch binder, it is classified as PG64-22 (true PG 64.88-24.7)
5.5 weight % linear styrene's butadiene styrene (SBS)
0.09 weight % elementary sulfur (being used as SBS crosslinking agents in asphalt binder)
Corn oil (RCO) is reclaimed in the vulcanization of the 2.0 weight % as described in embodiment #3.
Blending program：
1. after binder is annealed 1 hour at 150 DEG C, modifying agent is blended into pitch.Modified binder is added
Heat is used for polymer modification to about 193 DEG C.
2. the RPM in high-shear mixer is set as 1000, while adding SBS (in 1 minute).Add after polymer and stand
RPM is briefly tiltedly increased to 3000rpm, continues about 10 minutes, to ensure the complete decomposition of SBS beads, will cut afterwards
The level of cutting is reduced to 1000rpm.
3. continuing polymer blending under 1000rpm continues 2 hours altogether.
4. reducing the temperature to about 182 DEG C under 150rpm, sulfur crosslinking agent is now added.
5. continue to be blended 2 hours under 182 DEG C and 150rpm.
6. polymerization binder is placed in 150 DEG C of baking oven about 12-15 hours (staying overnight) so that polymer complete swelling.
Performance level estimate is carried out according to AASHTO M320.According to AASHTO T350, to the unaged knot at 76 DEG C
Material is closed above and to the RTFO residues at 64 DEG C to carry out many creeps under variable stress and recover to test.As a result show, for containing modification
For the binder of agent, although modulus is reduced, the average recovery percentage increase of binder, this demonstrate modifying agent conduct
The effect of SBS bulking agent so that produce the elastomer polymer of phase homogenous quantities has compared with the binder without modifying agent
Preferably distribution, and therefore there is more efficient elastomeric network.Details is shown in table 11.
Table 11
Embodiment 12：The regeneration of height aged asphalt binder is carried out using embodiment #3 oil
Example shown in Fig. 1 shows the complex modulus (G of the function as the Loading frequency reduced of pitch*) curve, abide by
Follow what ASTM D7175 were measured using dynamic shear rheometer (DSR).After laboratory aging to three kinds of levels, to embodiment #3
The sample of the middle asphalt binder (PG64-22) used is measured：
Ageing level 1：The deterioration by oxidation carried out 85 minutes in rolling film baking oven at 163 DEG C (follows ASTM
D2872)。
Ageing level 2：Ageing level under 2.1MPa air pressures is made at 100 DEG C by using pressure aging vessel PAV
Sample after 1 carries out the deterioration by oxidation of 20 hours and continues to aging (following ASTM D6521).According to grading performance specification,
PAV agings accelerate the simulation aging generally occurred during bituminous paving service life for 20 hours.
Ageing level 3：The sample after ageing level 1 and 2 is set to carry out 20 again by using pressure aging vessel PAV (PAV) small
When deterioration by oxidation and aging is continued to reach the PAV agings of 40 hours altogether, this represent the road from serious aging
The ageing level of the binder in face.
Fig. 1 is shown, from level 1 to level 2, and additional aging so that in the frequency entirely reduced from level 2 to level 3
Complex modulus in spectrum is dramatically increased.
By the way that binder is heated into 150 DEG C, continue 1 hour, and be blended in the summary of 5 weight % embodiment #3 oil
Close the asphalt binder for carrying out " regeneration " ageing level 3 in material.Shown corresponding to the curve of the regeneration binder in Fig. 1, it is described again
The raw G that aged asphalt is significantly reduced on whole spectral range*So that there is binder significantly less aged asphalt to combine
The rheological behavior of material.
Embodiment 13：The regeneration of height aged asphalt binder is carried out using embodiment #4 oil
Example shown in Fig. 1 shows the complex modulus (G of the function as the Loading frequency reduced of pitch*) curve, abide by
Follow what ASTM D7175 were measured using dynamic shear rheometer (DSR).To in the laboratory aging described in embodiment 12 to three kinds
The sample of the asphalt binder used in embodiment #3 (PG64-22) after level is measured, as it was previously stated, showing extra
Aging make it that complex modulus is dramatically increased on the frequency spectrum entirely reduced.
By the way that binder is heated into 150 DEG C, continue 1 hour, and be blended in the summary of 5 weight % embodiment #4 oil
Close the asphalt binder for carrying out " regeneration " ageing level 3 in material.Shown corresponding to the curve of the regeneration binder in Fig. 2, it is described again
The raw G that aged asphalt is significantly reduced on whole spectral range*So that binder has less aged asphalt binder
Rheological behavior.
Embodiment 14：Influence of the sulfurized oil to glass transition
The cryogenic property of pitch shown and significantly affected by asphalt vitrification transition temperature, and this will in the winter time (about -5
DEG C to -40 DEG C) occur in the range of the performance temperature that is often subjected to.In addition, the speed of pitch physical hardening has also been shown and pitch
Glass transition it is closely related, wherein flank speed occurs at Tg.Therefore, it is desirable to low glass transition temperature with
Reduction pitch reaches the possibility of its glass transition during its service life.Known aging can increase the vitrifying of pitch
Transition temperature, therefore the desired properties of effective regenerative agent are once incorporation, then reduce the glass transition of aged asphalt.
After significant laboratory aging, first time measurement is carried out to PG64-22 asphalt binders.Laboratory aging includes
The deterioration by oxidation of progress 85 minutes in rolling film baking oven (ASTM D2872) at 163 DEG C, is then held using pressure aging
The deterioration by oxidation of device (following ASTM D6521) progress 40 hours under 2.1MPa air pressures at 100 DEG C, this represent come
From the ageing level of the binder on the road surface of serious aging.The sample is labeled as " aged asphalt " in Fig. 1.
Included labeled as second sample of " aged asphalt+godied oil "：
The 95 weight % pure binders of foregoing PG58-28
Corn oil (RCO) is reclaimed in 5 weight % vulcanization, and its elementary sulfur under nitrogen jet with 1.5 weight % is 160
Reacted 7 hours at DEG C.This obtains the modifying agent with 16.0% oligomer and about 1.50 PDI.
Show that modifying agent makes the Tg of aged asphalt notable using the heat analysis of the binder before and after polymerization oil regeneration
Ground is moved to relatively low temperature, as shown in table 12.DSC is more as shown in Figure 3 than the comparison of heating curve.
Table 12
| Material is described | Glass transition temperature (DEG C) |
| Aged asphalt | -17 |
| Aged asphalt+godied oil | -27 |
Claims (66)
1. a kind of biorenewable of polymerization, previous modification or function carburetion (" godied oil "), it includes：
(a) there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
(b) scope is the polydispersity index of about 1.30 to about 2.20；And
(c) scope is 0.001 weight % to about 8 weight % sulfur content.
2. godied oil as claimed in claim 1, wherein the distribution of polymer has about 15 weight % to about 60 weight %'s
Oligomer.
3. godied oil as claimed in claim 1, wherein the polydispersity index scope is about 1.50 to about 2.05.
4. godied oil as claimed in claim 1, wherein the sulfur content is less than about 6 weight %.
5. godied oil as claimed in claim 1, wherein the sulfur content is less than about 4 weight %.
6. godied oil as claimed in claim 1, wherein the sulfur content is less than about 2 weight %.
7. godied oil as claimed in claim 1, it has the flash-point that scope is about 100 DEG C to about 400 DEG C.
8. godied oil as claimed in claim 1, it has the flash-point that scope is about 200 DEG C to about 350 DEG C.
9. godied oil as claimed in claim 1, it has the flash-point that scope is about 245 DEG C to about 275 DEG C.
10. godied oil as claimed in claim 1, wherein the godied oil derives from rising selected from the group being made up of the following
Beginning oil plant：Palm oil, sunflower oil, corn oil, soybean oil, Tower rape oil, rapeseed oil, Linseed oil, tung oil, castor-oil plant
Oil, tall oil, cottonseed oil, peanut oil, safflower oil, maize alcohol stillage oil and combinations thereof and rough stream.
11. godied oil as claimed in claim 1, wherein the godied oil derives from the starting oil plant comprising Arrcostab.
12. godied oil as claimed in claim 11, wherein the godied oil is derived from selected from the group being made up of the following
Originate oil plant：Methyl esters, ethyl ester, propyl ester and butyl ester and combinations thereof.
13. godied oil as claimed in claim 1, wherein the godied oil is from the starting oil plant being previously modified.
14. godied oil as claimed in claim 1, wherein the godied oil derives from rising selected from the group being made up of the following
Beginning oil plant：Triacylglyceride, diacylglycerol ester, monoacylglycerol ester and combinations thereof.
15. godied oil as claimed in claim 1, wherein the godied oil derives from the starting oil plant comprising phosphatide.
16. godied oil as claimed in claim 1, wherein the godied oil derives from the starting oil plant comprising animal tallow.
17. godied oil as claimed in claim 1, wherein the godied oil is derived from comprising the starting oil plant for reclaiming corn oil.
18. godied oil as claimed in claim 1, wherein the godied oil derives from the starting oil plant comprising free fatty.
19. godied oil as claimed in claim 1, wherein the godied oil derives from the starting oil plant comprising part hydrogenated oil and fat.
20. a kind of modified pitch, it includes godied oil as claimed in claim 1.
21. the modified pitch used in a kind of composition for paving the way, it includes godied oil as claimed in claim 1.
22. the modified pitch used in a kind of composition for spreading roof Material, it is comprising as claimed in claim 1 poly-
Close oil.
23. a kind of regenerative agent used in pitch, it includes godied oil as claimed in claim 1.
24. a kind of performance rate modifier used in pitch, it includes godied oil as claimed in claim 1.
25. a kind of bulking agent used in pitch, it includes godied oil as claimed in claim 1.
26. godied oil as claimed in claim 1, its also comprising come free thermoplastic elastomer (TPE) and thermoplastic polymer, polyphosphoric acid,
At least one of the group of antistripping additive, warm-mixing additive and fiber composition.
27. a kind of polymeric biological is renewable, the method for previous modification or function carburetion, it includes：
(a) biorenewable, previous modification or function carburetion are heated at least 100 DEG C；
(b) sulfur-containing compound is added into the oil of the heating；And
(c) make the sulfur-containing compound with the oil reaction to produce godied oil, it includes：
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. scope is sulfur contents of the about 0.001 weight % to about 8 weight %.
28. method as claimed in claim 27, it also includes step (d), passes through stream containing gas during step (c) described
Reactant mixture.
29. method as claimed in claim 28, wherein the gassiness body stream is selected from what is be made up of nitrogen, air and inert gas
Group.
30. method as claimed in claim 27, wherein the oil is heated at least 115 DEG C in step (a).
31. method as claimed in claim 27, wherein the sulfur-containing compound is added in solid form.
32. method as claimed in claim 27, wherein the sulfur-containing compound is added in molten form.
33. method as claimed in claim 27, wherein the sulfur-containing compound is the sulphur of reduction form.
34. method as claimed in claim 27, wherein the sulfur-containing compound is elementary sulfur.
35. method as claimed in claim 27, it adds accelerator after being additionally included in step (b).
36. method as claimed in claim 27, wherein the oligomer scope is about 15 weight % to about 60 weight %.
37. method as claimed in claim 27, wherein the polydispersity index scope is about 1.50 to about 2.05.
38. method as claimed in claim 27, wherein the sulfur content is less than about 6 weight %.
39. method as claimed in claim 27, wherein the sulfur content is less than about 4 weight %.
40. method as claimed in claim 27, wherein the sulfur content is less than about 2 weight %.
41. method as claimed in claim 27, wherein the godied oil has the flash-point that scope is about 100 DEG C to about 400 DEG C.
42. method as claimed in claim 27, wherein the godied oil has the flash-point that scope is about 200 DEG C to about 350 DEG C.
43. method as claimed in claim 27, wherein the godied oil has the flash-point that scope is about 245 DEG C to about 275 DEG C.
44. a kind of modified pitch, it includes the godied oil prepared according to claim 27.
45. the modified pitch used in a kind of composition for paving the way, it is included according to prepared by claim 27
Godied oil.
46. the modified pitch used in a kind of composition for spreading roof Material, it includes and prepared according to claim 27
The godied oil.
47. a kind of regenerative agent used in pitch, it includes the godied oil prepared according to claim 27.
48. a kind of performance rate modifier used in pitch, it includes the godied oil prepared according to claim 27.
49. a kind of bulking agent and sweller used in pitch, it includes the godied oil prepared according to claim 27.
50. a kind of warm-mixing additive used in pitch, it includes the godied oil prepared such as claim 27.
51. a kind of modified pitch, it is included：
(a) about 60 weight % to about 99.9 weight % asphalt binder；And
(b) about 0.1 weight % is to about 40 weight % godied oil, and it includes
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. it is less than about 8 weight % sulfur content.
52. modified pitch as claimed in claim 51, wherein the asphalt binder is used for pavement applications.
53. modified pitch as claimed in claim 51, wherein the asphalt binder is used to spread rooftop applications.
54. modified pitch as claimed in claim 51, wherein the asphalt binder is used for application.
55. modified pitch as claimed in claim 51, it is also comprising next free thermoplastic elastomer (TPE) and thermoplastic polymer, many phosphorus
At least one for the group that acid, antistripping additive, warm-mixing additive, emulsifying agent and fiber are constituted.
56. a kind of modified pitch, it is included：
(a) about 60 weight % to about 99.9 weight % asphalt binder；And
(b) about 0.1 weight % to about 40 weight % godied oil and unmodified biorenewable be oily, previous modification or functionalization
The blend of oil, wherein the godied oil has
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. it is less than about 8 weight % sulfur content.
57. modified pitch as claimed in claim 56, it is also comprising next free thermoplastic elastomer (TPE) and thermoplastic polymer, many phosphorus
At least one for the group that acid, antistripping additive, warm-mixing additive, emulsifying agent and fiber are constituted.
58. a kind of method that godied oil is mixed in asphalt applications, it includes：
(a) godied oil is obtained, it includes：
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. it is less than about 8 weight % sulfur content；And
(b) godied oil is added to asphalt binder, so as to obtain modified pitch；The scope of the amount of wherein described godied oil
For the 0.1 weight % to 40 weight % of the modified pitch.
59. a kind of method that godied oil is mixed in asphalt applications, it includes：
(a) godied oil is obtained, it includes：
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. it is less than about 8 weight % sulfur content；And
(b) godied oil is added to and is ready to use in gathering materials in bituminous paving, so as to obtain modified pitch；Wherein described polymerization
The scope of the amount of oil is the 0.1 weight % to 40 weight % of the modified pitch.
60. a kind of method that godied oil is mixed in asphalt applications, it includes：
(a) godied oil is obtained, it includes：
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. it is less than about 8 weight % sulfur content；And
(b) godied oil is added to and is ready to use in gathering materials in pitch paving roof, so as to obtain modified pitch；It is wherein described poly-
The scope for closing the amount of oil is the 0.1 weight % to 40 weight % of the modified pitch.
61. a kind of method that godied oil is mixed in asphalt applications, it includes：
(a) godied oil is obtained, it includes：
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. it is less than about 8 weight % sulfur content；And
(b) godied oil is added to before asphalt is applied and is ready to use in gathering materials in asphalt paint, so that the once collection
Material just obtains modified pitch with asphalt blending；The scope of the amount of wherein described godied oil is 0.1 weight of the modified pitch
Measure %-40 weight %.
62. a kind of method that godied oil is mixed in asphalt applications, it includes：
(a) godied oil is obtained, it includes：
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. it is less than about 8 weight % sulfur content；And
(b) godied oil is added to handle the recovery bituminous paving milling material (RAP) in bituminous paving to be reused for, so that
Obtain modified pitch；The scope of the amount of wherein described godied oil is the 0.1 weight %-40 weights of the modification and the pitch of regeneration
Measure %.
63. method as claimed in claim 62, it is also included the recovery bituminous paving milling material of the processing and asphalt
Blending.
64. a kind of method that godied oil is mixed in asphalt applications, it includes：
(a) godied oil is obtained, it includes：
Iv. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
V. scope is the polydispersity index of about 1.30 to about 2.20；And
Vi. it is less than about 8 weight % sulfur content；And
(b) godied oil is added to the emulsion for including water, emulsifying agent, asphalt and thermoplastic polymer.
65. the method as described in claim 64, it also includes reclaiming pitch with the emulsion processing with the godied oil
Road milling material (RAP), wherein the RAP of the processing is reused in bituminous paving or be applied to the table of existing bituminous paving
Face, so that the pitch for being modified and being regenerated；The scope of the amount of wherein described godied oil is the modification and the pitch of regeneration
0.1 weight % to 40 weight %.
66. a kind of method that godied oil is mixed in asphalt applications, it includes：
(a) godied oil is obtained, it includes：
I. there are about 2 weight % to the distribution of polymer of about 80 weight % oligomer；
Ii. scope is the polydispersity index of about 1.30 to about 2.20；And
Iii. it is less than about 8 weight % sulfur content；And
(b) godied oil is added to pitch as warm-mixing additive and/or compacting auxiliary agent, so as to obtain modified pitch；Its
Described in warm-mixing additive scope be modified pitch about 0.1 weight % to about 2 weight %.
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Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2976950A1 (en) | 2015-02-27 | 2016-09-01 | Cargill, Incorporated | Rejuvenating compositions for asphalt applications & methods of manufacturing the same |
| CA3015354C (en) | 2016-02-26 | 2024-04-02 | Cargill, Incorporated | Polymerized oils & methods of manufacturing the same |
| US10961395B2 (en) | 2016-02-29 | 2021-03-30 | Iowa State University Research Foundation, Inc. | Rejuvenation of vacuum tower bottoms through bio-derived materials |
| AT519266B1 (en) * | 2017-04-05 | 2018-05-15 | Oesterreichische Vialit Ges M B H | Street banquet and process for its manufacture |
| CA3059912C (en) | 2017-04-12 | 2023-03-21 | Cargill, Incorporated | Rejuvenating compounds in high performance asphalt compositions with high recycled content |
| CZ2017346A3 (en) * | 2017-06-16 | 2018-08-01 | České vysoké učenà technické v Praze - fakulta stavebnà | An asphalt mixture reinforced with plant fibres |
| US20200277496A1 (en) * | 2017-11-13 | 2020-09-03 | Stichting Wageningen Research | Lignin-based bio-asphalt |
| US11124926B2 (en) | 2018-02-02 | 2021-09-21 | Kraton Polymers Llc | Pavement repair method and system thereof |
| US11634875B2 (en) | 2018-02-02 | 2023-04-25 | Iemulsions Corporation | Pavement repair method and system thereof |
| CN109142148A (en) * | 2018-07-27 | 2019-01-04 | 北京建筑大学 | A method of based on CAM model analysis THFS modified pitch temperature-sensitive performance |
| CN109534722A (en) * | 2018-10-09 | 2019-03-29 | 中国石油化工股份有限公司 | A kind of high-performance reclaimed bituminous pavement cold-repairing material and preparation method thereof |
| US11518910B2 (en) | 2018-10-25 | 2022-12-06 | Poet Research, Inc. | Bio-based additive for asphalt |
| US11965336B2 (en) | 2019-01-10 | 2024-04-23 | Bmic Llc | Non-asphaltic coatings, non-asphaltic roofing materials, and methods of making thereof |
| US11814506B2 (en) | 2019-07-02 | 2023-11-14 | Marathon Petroleum Company Lp | Modified asphalts with enhanced rheological properties and associated methods |
| CN110551402B (en) * | 2019-08-09 | 2021-12-03 | 河南省高远公路养护技术有限公司 | Normal-temperature regenerant for waste asphalt mixture and preparation method thereof |
| CA3149052A1 (en) | 2019-09-18 | 2021-03-25 | Eric W. Cochran | Biosolvents useful for improved asphalt products utilizing recycled asphalt pavement or other brittle asphalt binders such as vacuum tower bottom |
| US11401449B2 (en) | 2019-09-23 | 2022-08-02 | Bmic Llc | Methods of forming an adhesive composition from asphalt shingle waste powder |
| US11702801B2 (en) | 2019-09-30 | 2023-07-18 | Owens Corning Intellectual Capital, Llc | Methods and compositions for asphalt rejuvenation |
| US20230034141A1 (en) * | 2019-11-20 | 2023-02-02 | Cargill, Incorporated | Binder composition including bio-based component |
| CN111576162A (en) * | 2020-05-13 | 2020-08-25 | 内蒙古路桥集团有限责任公司 | Emulsified asphalt plant-mixed cold-recycling pavement construction process |
| US20230374310A1 (en) * | 2020-09-29 | 2023-11-23 | Arizona Board Of Regents On Behalf Of Arizona State University | In-situ polymerization of sulfur and bio-oils in bituminous matrices |
| CA3217405A1 (en) | 2021-05-06 | 2022-11-10 | Sung AHN | Epoxy functional and phospholipid containing adhesion promoters and warm mix additives for asphalt applications |
| CN113667313A (en) * | 2021-08-17 | 2021-11-19 | 浙江交通资源投资有限公司沥青科技分公司 | Special molecular dense maintenance asphalt and preparation method thereof |
| EP4296308A1 (en) | 2022-06-24 | 2023-12-27 | LANXESS Deutschland GmbH | Compounds containing bitumen, method for their preparation and their use |
| WO2024097963A1 (en) * | 2022-11-04 | 2024-05-10 | Cargill, Incorporated | Sulfurized stabilizers for use in epoxy functional and phospholipid containing compositions for asphalt applications |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009137298A1 (en) * | 2008-05-06 | 2009-11-12 | Archer Daniels Midland Company | Lubricant additives |
| CN104204014A (en) * | 2012-01-18 | 2014-12-10 | 爱荷华州立大学研究基金会有限公司 | Thermoplastic elastomers via atom transfer radical polymerization of plant oil |
Family Cites Families (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1315246A (en) * | 1919-09-09 | Process of treating vulcanized oils and product thereof | ||
| US1833471A (en) * | 1927-09-09 | 1931-11-24 | Du Pont | Coated fabric and method of preparing same |
| US2152185A (en) * | 1934-03-26 | 1939-03-28 | Karl Werner Posnansky | Process for sulphurizing organic compounds having unsaturated linkages of an aliphatic character |
| US2390961A (en) * | 1943-07-13 | 1945-12-11 | Sanderson Donald | Polymerized rubberlike product and process of making the same |
| US2450384A (en) * | 1945-02-13 | 1948-09-28 | Anchor Chemical Company Ltd | Manufacture of factice and sulfurized oils |
| US2817653A (en) * | 1950-04-27 | 1957-12-24 | Texas Co | Sulfur-containing polymers |
| US2750298A (en) | 1952-04-10 | 1956-06-12 | Glidden Co | Solution of resin in blown oil treated with friedel-crafts catalyst to produce varnish |
| US2815296A (en) * | 1954-05-27 | 1957-12-03 | Exxon Research Engineering Co | Asphalt composition containing a liquid hydrogenated polymer oil |
| US3378506A (en) | 1963-10-07 | 1968-04-16 | Dayco Corp | Elastomeric porous material and method for manufacturing same |
| FR1423702A (en) * | 1964-08-07 | 1966-01-07 | Citroen Sa Andre | Automatic gearbox with converter |
| US3595820A (en) * | 1968-10-14 | 1971-07-27 | Standard Oil Co | Process for enhancing the sulfur retention of sulfurized polybutenes |
| GB1226234A (en) * | 1969-02-13 | 1971-03-24 | ||
| JPS498017B1 (en) * | 1969-09-16 | 1974-02-23 | ||
| BR7700094A (en) * | 1976-09-17 | 1978-06-06 | Vinoxen Co | PROCESS TO ELIMINATE OR REDUCE THE DESIRE TO SMOKE |
| JPS5626405Y2 (en) | 1977-02-15 | 1981-06-23 | ||
| JPS5914504B2 (en) | 1978-01-17 | 1984-04-04 | 日瀝化学工業株式会社 | Bituminous composition for pavement |
| US4226552A (en) * | 1978-05-17 | 1980-10-07 | Moench Frank F | Asphaltic pavement treating apparatus and method |
| US4298397A (en) * | 1979-01-08 | 1981-11-03 | Burris Michael V | Asphalt-sulfur emulsion composition |
| JPS5842610A (en) * | 1981-09-07 | 1983-03-12 | Mitsui Petrochem Ind Ltd | Hydrocarbon resin and its modified product |
| GB8426007D0 (en) * | 1984-10-15 | 1984-11-21 | Shell Int Research | Binder composition |
| SU1298214A1 (en) * | 1985-07-17 | 1987-03-23 | Волгоградский Политехнический Институт | Method for producing factice |
| US4740322A (en) * | 1985-07-29 | 1988-04-26 | The Lubrizol Corporation | Sulfur-containing compositions, and additive concentrates, lubricating oils, metal working lubricants and asphalt compositions containing same |
| ZA865342B (en) | 1985-07-29 | 1987-03-25 | Lubrizol Corp | Sulfur-containing compositions and additive concentrates,lubricating oils,metal working lubricants and asphalt compositions containing same |
| US5691284A (en) * | 1990-08-11 | 1997-11-25 | Rohm Gmbh | Synthetic oligomeric oils |
| JPH0498017A (en) | 1990-08-17 | 1992-03-30 | Matsushita Electric Ind Co Ltd | Electric stove |
| BR9504838A (en) * | 1994-11-15 | 1997-10-07 | Lubrizol Corp | Polyol ester lubricating oil composition |
| JP3957389B2 (en) * | 1998-02-13 | 2007-08-15 | 昭和シェル石油株式会社 | Asphalt emulsion |
| US6117227A (en) * | 1998-04-28 | 2000-09-12 | Hikarigiken Co., Ltd. | Asphalt paving mix formed of recycled asphalt concrete and new asphalt for paving at ambient temperatures and a process for making the same |
| US6133351A (en) * | 1999-06-03 | 2000-10-17 | Marathon Ashland Petroleum Llc | Sulfur-in-oil in asphalt and polymer composition and process |
| AU2001234890A1 (en) * | 2000-02-08 | 2001-08-20 | Waste Technology Transfer, Inc. | Petroleum asphalts modified by liquefied biomass additives |
| WO2001074948A1 (en) * | 2000-03-30 | 2001-10-11 | University Of Alaska Fairbanks | Construction materials and soil stabilization using vegetable oil |
| CA2315955A1 (en) | 2000-08-08 | 2002-02-08 | Q-X Enviro Products Ltd. | Dust control composition |
| US8639849B2 (en) | 2001-12-17 | 2014-01-28 | Sutech Data Solutions Co., Llc | Integrated circuits for high speed adaptive compression and methods therefor |
| US7842746B2 (en) * | 2002-05-02 | 2010-11-30 | Archer-Daniels-Midland Company | Hydrogenated and partially hydrogenated heat-bodied oils and uses thereof |
| US6749677B2 (en) | 2002-08-07 | 2004-06-15 | Michael Freisthler | Asphalt sealer composition |
| US6956071B2 (en) * | 2002-12-20 | 2005-10-18 | Fina Technology, Inc. | Use of alternate thiol accelerators for crosslinking rubber in asphalt |
| US7517934B2 (en) * | 2003-07-31 | 2009-04-14 | Basf Corporation | Modified anionically polymerized polymers |
| CN1942525B (en) * | 2004-02-18 | 2010-05-26 | 米德维斯特沃克公司 | Method for producing bituminous compositions |
| US7833338B2 (en) | 2004-02-18 | 2010-11-16 | Meadwestvaco Packaging Systems, Llc | Method for producing bitumen compositions |
| AU2005267131A1 (en) | 2004-06-25 | 2006-02-02 | Andrew Guo | Modified vegetable oil-based polyols |
| US20060089429A1 (en) * | 2004-10-22 | 2006-04-27 | Fina Technology, Inc. | Use of inorganic acids with crosslinking agents in polymer modified asphalts |
| US20060121170A1 (en) * | 2004-12-06 | 2006-06-08 | Howard David L | Rubbery gels made from vegetable oils |
| US6987207B1 (en) * | 2005-03-03 | 2006-01-17 | Alan Jeffrey Ronyak | Hydrocarbonaceous composition |
| MX2007013271A (en) | 2005-04-25 | 2008-01-21 | Cargill Inc | Polyurethane foams comprising oligomeric polyols. |
| US20070105987A1 (en) * | 2005-11-04 | 2007-05-10 | Latexfalt B.V. | Binder composition comprising a low viscosity naphthenic oil for coloured hot-mix asphalt applications |
| US20100261805A1 (en) * | 2006-03-27 | 2010-10-14 | Abraham Timothy W | Oligomeric polyols from palm-based oils and polyurethane compositions made therefrom |
| DE102006038614A1 (en) | 2006-08-17 | 2008-02-21 | Norddeutsche Mischwerke Gmbh & Co. Kg | Process for reuse of spent asphalts and production of bituminous mixtures |
| US7501479B2 (en) | 2007-05-07 | 2009-03-10 | Pittsburg State University | Cationic polymerization of biological oils with superacid catalysts |
| GB2462322A (en) | 2008-08-05 | 2010-02-10 | Aggregate Ind Uk Ltd | Asphalt Rejuvenation |
| WO2010016127A1 (en) * | 2008-08-07 | 2010-02-11 | Dic株式会社 | Additive for lubricating fluid, lubricating fluid composition and method for producing sulfurized polyolefin |
| WO2010077141A1 (en) * | 2009-01-05 | 2010-07-08 | Rasenberg Wegenbouw B.V. | Asphalt composition |
| FR2945816B1 (en) * | 2009-05-19 | 2011-08-26 | Total Raffinage Marketing | BITUMINOUS BINDER FOR PREPARING ASPHALT OR COATING AT LOW TEMPERATURES |
| US8779172B2 (en) | 2009-05-22 | 2014-07-15 | Cargill, Incorporated | Corn stillage oil derivatives |
| US8765985B2 (en) * | 2009-05-22 | 2014-07-01 | Cargill, Incorporated | Blown corn stillage oil |
| US20110146531A1 (en) | 2009-12-17 | 2011-06-23 | 3M Innovative Properties Company | Bituminous compositions and methods |
| US8227399B2 (en) * | 2010-02-12 | 2012-07-24 | Evonik Goldschmidt Gmbh | Polyglycerol esters and their use |
| US7951417B1 (en) * | 2010-04-05 | 2011-05-31 | United Environment & Energy Llc | Bio-based adhesive material for roof shingles |
| GB2480103B (en) | 2010-05-07 | 2012-10-10 | Reckitt & Colman Overseas | Aerosol compositions |
| WO2011146848A1 (en) | 2010-05-21 | 2011-11-24 | Cargill, Incorporated | Blown and stripped blend of soybean oil and corn stillage oil |
| BR112012029618B1 (en) | 2010-05-21 | 2021-09-28 | Cargill, Incorporated | METHODS FOR THE PRODUCTION OF A PLANT-BASED OIL |
| US8152407B1 (en) | 2010-11-08 | 2012-04-10 | Saudi Arabian Oil Company | Auxiliary pressure relief reservoir for crash barrier |
| CA2837073C (en) * | 2011-05-27 | 2020-04-07 | Cargill, Incorporated | Bio-based binder systems |
| US9115295B2 (en) * | 2011-06-10 | 2015-08-25 | Colas | Vegetable-based products of the siccative type for recycling and rejuvenating reclaimed asphalt pavements in situ or in a dedicated plant |
| FR2981347B1 (en) * | 2011-10-12 | 2015-10-16 | Ceca Sa | ADDITIVE FOR COATS CONTAINING RECYCLED BITUMINOUS PRODUCTS |
| WO2013090283A1 (en) * | 2011-12-12 | 2013-06-20 | Arizona Chemical Company, Llc | Rejuvenation of reclaimed asphalt |
| MY165734A (en) * | 2012-04-26 | 2018-04-20 | Arizona Chemical Co Llc | Rejuvenation of reclaimed asphalt |
| JP5955119B2 (en) | 2012-06-15 | 2016-07-20 | 植田製油株式会社 | Method for producing edible fats and oils |
| EP2687739A1 (en) | 2012-07-20 | 2014-01-22 | Aktiebolaget SKF | Angular contact bearing assembly for use in a steering column |
| US8821064B1 (en) | 2013-02-20 | 2014-09-02 | Ergon Asphalt & Emulsions, Inc. | Acrylic-modified asphalt rejuvenating emulsion |
| US9688882B2 (en) * | 2013-03-15 | 2017-06-27 | Owens Corning Intellectual Capital, Llc | Use of an additive and paving grade asphalt in shingle coating asphalt composition manufacture |
| EP3327047A1 (en) * | 2013-05-20 | 2018-05-30 | Iowa State University Research Foundation, Inc. | Thermoplastic elastomers via reversible addition-fragmentation chain transfer polymerization of triglycerides |
| ES2729875T3 (en) * | 2014-03-14 | 2019-11-06 | Cargill Inc | Biorenovable blown and distilled oils for use in the asphalt industry |
| CA2976950A1 (en) | 2015-02-27 | 2016-09-01 | Cargill, Incorporated | Rejuvenating compositions for asphalt applications & methods of manufacturing the same |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009137298A1 (en) * | 2008-05-06 | 2009-11-12 | Archer Daniels Midland Company | Lubricant additives |
| CN104204014A (en) * | 2012-01-18 | 2014-12-10 | 爱荷华州立大学研究基金会有限公司 | Thermoplastic elastomers via atom transfer radical polymerization of plant oil |
Non-Patent Citations (2)
| Title |
|---|
| 刘尚乐: "《石油沥青及其在建筑中应用》", 30 June 1983, 中国建筑工业出版社 * |
| 赵晓云 等: "等离子体聚合废植物油及其润滑性能", 《华东理工大学学报（自然科学版）》 * |
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